Flights
Meals unless stated
Travel Insurance
Day 1 – Saturday, July 25: Depart for Pittsburgh
Make your way to our host hotel the Holiday Inn Express & Suites North Shore, Pittsburgh, ideally located just a five-minute walk from PNC Park and surrounded by many of Pittsburgh’s best bars and restaurants. Make sure you plan to arrive no later than 2pm.
After checking in, we’ll head to PNC Park for our 3pm behind-the-scenes tour of this beautiful ballpark—home of the Pittsburgh Pirates—before taking our seats for tonight’s 6.40pm matchup: Cubs vs. Pirates.
Day 2 – Sunday, July 26: Explore the Steel City
Enjoy breakfast (included each morning), then spend your free time discovering the best of Pittsburgh. Ride the historic Monongahela Incline for sweeping views over the city’s iconic Golden Triangle, or explore the rich athletic heritage of the region at the Western Pennsylvania Sports Museum.
We’ll reconvene at 11:45am for a short walk to PNC Park as the Chicago Cubs face off once again against the Pittsburgh Pirates in Game 2 of the series, at 1.35pm
Day 3 – Monday, July 27: On to Cincinnati
After breakfast, we check out and travel west to Cincinnati, where we’ll stay two nights at the Fairfield Inn & Suites. Relax and unwind before heading to The Great American Ball Park to watch the Cincinnati Reds face off against the Cleveland Guardians at 7.10pm
Day 4 – Tuesday, July 28: Louisville Excursion
This morning, we journey south to Louisville, Kentucky, for two iconic visits. Our first stop is Churchill Downs and the Kentucky Derby Museum, where a short guided track tour brings to life “the most exciting two minutes in sports.”
Next, we visit the Louisville Slugger Museum & Factory. After a boxed lunch, enjoy a tour of the legendary baseball bat factory and time to explore exhibits, take photos, and pick up souvenirs.
In the evening, we return to Cincinnati for Game 2 of the Reds–Guardians series, again at 7.10pm
Day 5 – Wednesday, July 29: The Windy City Awaits
We’re back on the road this morning, heading north to Chicago. Upon arrival, check into the Hyatt Place, then get ready for an exciting evening game at Guaranteed Rate Field, where the New York Yankees take on the Chicago White Sox at 6.40pm
Day 6 – Thursday, July 30: Field of Dreams & Rockford Peaches
It’s an early start for an unforgettable day trip! We travel to Dyersville, Iowa, to visit the Field of Dreams Movie Site—a must-see for every baseball fan. Enjoy a nostalgic experience playing catch on the iconic diamond, walking through the cornfield, and touring the farmhouse featured in the movie. A lunch on-site is included.
On our way back to Illinois, we’ll stop in Rockford, home of the legendary Rockford Peaches from A League of Their Own. Visit Beyer Stadium, now being lovingly restored, and explore the museum celebrating the women of the All-American Girls Professional Baseball League.
After this memorable day, we return to Chicago for a well-earned rest.
Day 7 – Friday, July 31: Wrigley Field & Yankees–Cubs Showdown
After a relaxed breakfast, enjoy a morning behind-the-scenes tour of historic Wrigley Field, one of baseball’s most beloved ballparks. Then we stay at the ballpark for the lunchtime blockbuster game, as the Yankees take on the Cubs at 1.20pm. The evening is free to explore Chicago—perhaps stroll along the Magnificent Mile or enjoy an evening river cruise.
Day 8 – Saturday, August 1: Bound for Cleveland
After an early breakfast, we depart for Cleveland and check in at Tru by Hilton Cleveland Midtown for our final two nights.
From there, we make our way straight to Progressive Field for an exclusive behind-the-scenes tour before settling in to watch the Cleveland Guardians take on the Arizona Diamondbacks at 7:15pm.
Day 9 – Sunday, August 2: Rock & Baseball History
After breakfast, we head to the world-famous Rock & Roll Hall of Fame, located on the Lake Erie waterfront. Then at lunchtime we head back to the ballpark for the Diamondbacks–Guardians Game 2 at 1.40pm —our final ballgame of the tour!
Day 10 – Monday, August 3: Homeward Bound
After one last breakfast together, we check out of the hotel and you head home, filled with great memories from this incredible baseball adventure.
We always recommend you take out Travel Insurance and below we've listed just some of the reasons why:
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| All pricing is per person | |
| Single 1 guest per room | 4899 USD |
| Double 2 guests per room | 3699 USD |
| Triple 3 guests per room | 3549 USD |
| Pay deposit only | 500 USD |
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